[(3R,5S)-5-acetyloxy-7-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)heptan-3-yl] acetate

Details

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Internal ID 56098e2c-f293-484b-a993-20758196ede2
Taxonomy Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids > Curcuminoids
IUPAC Name [(3R,5S)-5-acetyloxy-7-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)heptan-3-yl] acetate
SMILES (Canonical) CC(=O)OC(CCC1=CC(=C(C=C1)O)OC)CC(CCC2=CC(=C(C(=C2)OC)O)OC)OC(=O)C
SMILES (Isomeric) CC(=O)O[C@H](CCC1=CC(=C(C=C1)O)OC)C[C@H](CCC2=CC(=C(C(=C2)OC)O)OC)OC(=O)C
InChI InChI=1S/C26H34O9/c1-16(27)34-20(9-6-18-8-11-22(29)23(12-18)31-3)15-21(35-17(2)28)10-7-19-13-24(32-4)26(30)25(14-19)33-5/h8,11-14,20-21,29-30H,6-7,9-10,15H2,1-5H3/t20-,21+/m1/s1
InChI Key WMROZLOCVPCLGP-RTWAWAEBSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C26H34O9
Molecular Weight 490.50 g/mol
Exact Mass 490.22028266 g/mol
Topological Polar Surface Area (TPSA) 121.00 Ų
XlogP 4.30
Atomic LogP (AlogP) 3.94
H-Bond Acceptor 9
H-Bond Donor 2
Rotatable Bonds 13

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3R,5S)-5-acetyloxy-7-(4-hydroxy-3,5-dimethoxyphenyl)-1-(4-hydroxy-3-methoxyphenyl)heptan-3-yl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9342 93.42%
Caco-2 - 0.5690 56.90%
Blood Brain Barrier - 0.7250 72.50%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.9330 93.30%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9066 90.66%
OATP1B3 inhibitior - 0.2672 26.72%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior + 0.9601 96.01%
P-glycoprotein inhibitior + 0.7891 78.91%
P-glycoprotein substrate + 0.5614 56.14%
CYP3A4 substrate + 0.5526 55.26%
CYP2C9 substrate - 0.8108 81.08%
CYP2D6 substrate - 0.7795 77.95%
CYP3A4 inhibition - 0.7498 74.98%
CYP2C9 inhibition - 0.6356 63.56%
CYP2C19 inhibition + 0.5093 50.93%
CYP2D6 inhibition - 0.8831 88.31%
CYP1A2 inhibition + 0.5177 51.77%
CYP2C8 inhibition + 0.7142 71.42%
CYP inhibitory promiscuity - 0.8581 85.81%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.7797 77.97%
Carcinogenicity (trinary) Non-required 0.7431 74.31%
Eye corrosion - 0.9902 99.02%
Eye irritation - 0.8439 84.39%
Skin irritation - 0.8912 89.12%
Skin corrosion - 0.9698 96.98%
Ames mutagenesis - 0.8000 80.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6631 66.31%
Micronuclear - 0.6741 67.41%
Hepatotoxicity - 0.7750 77.50%
skin sensitisation - 0.9420 94.20%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.5667 56.67%
Mitochondrial toxicity - 0.6875 68.75%
Nephrotoxicity - 0.7706 77.06%
Acute Oral Toxicity (c) III 0.6317 63.17%
Estrogen receptor binding + 0.8654 86.54%
Androgen receptor binding + 0.6067 60.67%
Thyroid receptor binding + 0.7261 72.61%
Glucocorticoid receptor binding + 0.8986 89.86%
Aromatase binding + 0.6850 68.50%
PPAR gamma + 0.6891 68.91%
Honey bee toxicity - 0.8396 83.96%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.9891 98.91%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.78% 91.11%
CHEMBL2581 P07339 Cathepsin D 98.02% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.56% 96.09%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 95.94% 95.17%
CHEMBL3060 Q9Y345 Glycine transporter 2 94.45% 99.17%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.23% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.39% 86.33%
CHEMBL1255126 O15151 Protein Mdm4 88.09% 90.20%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 87.04% 99.15%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 85.28% 95.50%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.96% 94.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 84.13% 96.00%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 83.61% 90.71%
CHEMBL3401 O75469 Pregnane X receptor 83.20% 94.73%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.11% 95.56%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.51% 92.62%
CHEMBL5939 Q9NZ08 Endoplasmic reticulum aminopeptidase 1 82.20% 100.00%
CHEMBL2413 P32246 C-C chemokine receptor type 1 81.30% 89.50%
CHEMBL2535 P11166 Glucose transporter 81.25% 98.75%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Zingiber officinale

Cross-Links

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PubChem 163045339
LOTUS LTS0070218
wikiData Q105308802